Our Observation

Winter Park’s Bill Segal was all smiles as he watched the election results on Aug. 24. But he was on the verge of watching his political star fall from the sky.

In an election for Orange County mayor in which he and a political action committee had spent more than $1 million, the Orange County commissioner had just been beaten by someone who spent $217,000. And he didn’t just lose. He lost by nearly double the votes.

But that didn’t matter much to Segal, who was running in a four-candidate race for mayor, with the top two candidates going on to a runoff since none of them received the requisite 50 percent plus-one vote needed to win it all on Aug. 24.

He had come in No. 2, which was good enough for him. Against Commissioner Linda Stewart, with whom his vote count tangled for most of election night, he had lived through a nail-biter, picking up 22 percent of the vote to Stewart’s 19.

“We just wanted to get into the runoff, and we did it,” Segal said.

But a few points more could have cost Segal dearly, and handed former Orange County Commissioner Teresa Jacobs an instant win in an election that was otherwise expected to be a formality before the real runoff election would be held in November.

Jacobs won with 43 percent of the vote, not enough to win outright, but giving her the de facto front-runner position in the upcoming runoff against Segal.

Matthew Falconer, who had made political theater out of a lawsuit against Orange County over its SunRail financial agreement, finished fourth with 15 percent.

Nobody was expected to win more than 50 percent of the vote necessary to win the election for mayor on the spot.

If anybody, Segal, the well-known, politically savvy former developer-turned-commissioner, was expected to win. With a campaign war chest that nearly quintupled that of his second-closest rival, he certainly had the funding.

But the connections that helped him raise money in a hurry also helped his opponents cast him as the ultimate insider in the race.

Segal admittedly had been connected to the business and political elite of Orange County for 30 years, initially starting as a developer donating money and a volunteer serving on boards, before eventually deciding to get involved in the Legislature himself.

He blamed Jacobs’ popularity at the polls on her having energized her base in an election with a very low turnout. Only 20 percent of registered voters showed up to the polls for the Aug. 24 primaries, far less than expected in November.

And that, among other things, could prove a game changer for the Orange County mayoral election.

For one, it’s about to get a lot more partisan. Though candidates shied away from overtly partisan messages during the campaign, all four were connected directly with major parties. Jacobs and Falconer are longtime Republicans. Segal and Stewart are longtime Democrats.

With one from each political camp remaining, the numbers look daunting for the Democratic side, despite the vote frequently leaning Democratic in larger elections.

Republicans received 58 percent of the votes in the Orange County mayor race, versus 42 percent for Democrats.

“The people who turned out in this race were very partisan — these were Teresa’s voters,” Segal said just after coming in second in the primaries. “We’re looking for a better, more centrist electorate who are more representative of the people of Orange County.”

Come November, it could be a whole new ballgame.